A conformationally restricted cyclic pentapeptide, containing an unsaturated 9-membered lactam as a semi-rigid scaffold, was prepared in a very convergent manner, through tandem Ugi reaction/ring closing metathesis. A thorough conformational study with the aid of NMR was carried out on it. The promising properties of cyclic pentapeptides related to the one prepared have been demonstrated by the good yield achieved in macrocyclization, by the fact that the synthesized macrocyclic peptide seems to be conformationally defined, and by the probable presence of strong intramolecular hydrogen bonds corresponding to beta- and gamma-turns.
Application of tandem Ugi multi-component reaction/ring closing metathesis to the synthesis of a conformationally restricted cyclic pentapeptide
BANFI, LUCA;BASSO, ANDREA;DAMONTE, GIANLUCA;GUANTI, GIUSEPPE;RIVA, RENATA
2005-01-01
Abstract
A conformationally restricted cyclic pentapeptide, containing an unsaturated 9-membered lactam as a semi-rigid scaffold, was prepared in a very convergent manner, through tandem Ugi reaction/ring closing metathesis. A thorough conformational study with the aid of NMR was carried out on it. The promising properties of cyclic pentapeptides related to the one prepared have been demonstrated by the good yield achieved in macrocyclization, by the fact that the synthesized macrocyclic peptide seems to be conformationally defined, and by the probable presence of strong intramolecular hydrogen bonds corresponding to beta- and gamma-turns.File in questo prodotto:
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